Trimethyl methanetricarboxylate → HCID 71284563, compound

HRID 1481683Notes

Reaction equation

HRID 1481683 reaction equation
CC([N:5]=[C:6]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[CH2:15][CH2:14][CH2:13]2)[CH2:7][CH2:8][CH3:9])(C)C.[CH:21]([C:30]([O:32][CH3:33])=[O:31])([C:26](OC)=[O:27])[C:22](OC)=[O:23]>COCCOCCOC>[CH2:8]([C:7]1[C:22]([OH:23])=[C:21]([C:30]([O:32][CH3:33])=[O:31])[C:26](=[O:27])[NH:5][C:6]=1[C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH3:20])[CH2:15][CH2:14][CH2:13]2)[CH3:9]

Participants

4

Reactant 2

HCID 136922Trimethyl methanetricarboxylateHCID 89422940HCID 89422940, compound

Product 1

HCID 71284563HCID 71284563, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
160 °C

Procedure

To a suspension of 2-methyl-N-(1-(1-methyl-1,2,3,4-tetrahydroquinolin-6-yl)butylidene)propan-2-amine (1.96 g, ca. 7.2 mmol), prepared according to procedure described in Example 1 Step 6, in diglyme (7 mL) was added trimethyl methanetricarboxylate (2.33 g, 12.2 mmol, 1.7 eq). The reaction was stirred at 160° C. for 4 h then cooled to room temperature. The precipitate was collected by filtration then washed with Et2O to afford the title compound as a yellow solid (150 mg, 0.44 mmol, 6.5% over two steps).

Workup

  1. customprepared
  2. temperaturethen cooled to room temperature
  3. filtrationThe precipitate was collected by filtration
  4. washthen washed with Et2O

Sources & evidence

ORD record
ord-ba3124193fab48d2bad53031764d4ef1
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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